Generation and Aldehyde Addition of a Zinc Carbenoid Substituted by Fluorine

Synlett

Volumn 1996, Issue 9, 1996, Pages 831-832

  Hata, Takeshi ^a   Shimizu, Masaki ^a   Hiyama, Tamejiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008601714     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5623     Document Type: Article

References (30)

1. Reviews: (a) Welch, J. T. Tetrahedron 1987, 43, 3123. (b) Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Application;. Liebman, J. F.; Greenberg, A.; Dolbier, Jr. W, R., Eds.; VCH: New York, 1988. (c) Selective Fluorination in Organic and Bioorganic Chemistry, Welch, J. T.; Ed.; ACS Symposium Series 456; American Chemical Society, Washington, DC, 1991. (d) Organofluorine Chemistry. Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press, New York, 1994. (e) Chemistry of Organic Fluorine Compounds II. A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
2. Reviews: (a) Welch, J. T. Tetrahedron 1987, 43, 3123. (b) Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Application;. Liebman, J. F.; Greenberg, A.; Dolbier, Jr. W, R., Eds.; VCH: New York, 1988. (c) Selective Fluorination in Organic and Bioorganic Chemistry, Welch, J. T.; Ed.; ACS Symposium Series 456; American Chemical Society, Washington, DC, 1991. (d) Organofluorine Chemistry. Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press, New York, 1994. (e) Chemistry of Organic Fluorine Compounds II. A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
3. Reviews: (a) Welch, J. T. Tetrahedron 1987, 43, 3123. (b) Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Application;. Liebman, J. F.; Greenberg, A.; Dolbier, Jr. W, R., Eds.; VCH: New York, 1988. (c) Selective Fluorination in Organic and Bioorganic Chemistry, Welch, J. T.; Ed.; ACS Symposium Series 456; American Chemical Society, Washington, DC, 1991. (d) Organofluorine Chemistry. Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press, New York, 1994. (e) Chemistry of Organic Fluorine Compounds II. A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
4. Reviews: (a) Welch, J. T. Tetrahedron 1987, 43, 3123. (b) Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Application;. Liebman, J. F.; Greenberg, A.; Dolbier, Jr. W, R., Eds.; VCH: New York, 1988. (c) Selective Fluorination in Organic and Bioorganic Chemistry, Welch, J. T.; Ed.; ACS Symposium Series 456; American Chemical Society, Washington, DC, 1991. (d) Organofluorine Chemistry. Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press, New York, 1994. (e) Chemistry of Organic Fluorine Compounds II. A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
5. Reviews: (a) Welch, J. T. Tetrahedron 1987, 43, 3123. (b) Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Application;. Liebman, J. F.; Greenberg, A.; Dolbier, Jr. W, R., Eds.; VCH: New York, 1988. (c) Selective Fluorination in Organic and Bioorganic Chemistry, Welch, J. T.; Ed.; ACS Symposium Series 456; American Chemical Society, Washington, DC, 1991. (d) Organofluorine Chemistry. Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum Press, New York, 1994. (e) Chemistry of Organic Fluorine Compounds II. A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
6. For reviews of fluorinated organometallic reagents, see (a) Burton, D. J.; Yang, Z. Y. Tetrahedron 1992, 48, 189. (b) Burton, D. J.; Yang, Z. Y.; Morken, P. A. Tetrahedron 1994, 50, 2993.
7. For reviews of fluorinated organometallic reagents, see (a) Burton, D. J.; Yang, Z. Y. Tetrahedron 1992, 48, 189. (b) Burton, D. J.; Yang, Z. Y.; Morken, P. A. Tetrahedron 1994, 50, 2993.
8. (a) Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Synlett 1995, 987.
9. (b) Kuroboshi, M.; Yamada, N.; Takebe, Y.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6271.
10. For recent review of zinc carbenoid, see Motherwell, W. B.; Nutley, C. J. Contemporary Organic Synthesis 1994, 1, 219.
11. 2Zn as the reducing reagent, see (a) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1966, 28, 3353. (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53. For structual studies of (halomethyl)zinc reagents generated by Furukawa's method, see (c) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 723. (d) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114 , 2592.
12. 2Zn as the reducing reagent, see (a) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1966, 28, 3353. (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53. For structual studies of (halomethyl)zinc reagents generated by Furukawa's method, see (c) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 723. (d) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114 , 2592.
13. 2Zn as the reducing reagent, see (a) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1966, 28, 3353. (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53. For structual studies of (halomethyl)zinc reagents generated by Furukawa's method, see (c) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 723. (d) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114 , 2592.
14. 2Zn as the reducing reagent, see (a) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1966, 28, 3353. (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53. For structual studies of (halomethyl)zinc reagents generated by Furukawa's method, see (c) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 723. (d) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114 , 2592.
15. 2FO: C, 36.84; H, 3.40%, Found: C, 36.70; H, 3.55%.
16. The presence of LiBr is reported to stabilize a lithium carbenoid. Tarhouni, R.; Kirschleger, B.; Rambaud, M.; Villieras, J. Tetrahedron Lett. 1984, 25, 835.
17. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
18. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
19. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
20. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
21. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
22. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
23. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
24. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
25. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
26. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
27. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
28. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
29. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.
30. For examples of discrimination between aldehydes and ketones by organometallic reagents, see B: (a) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544. Mg: (b) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 342. Cr: (c) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (d) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561. (e) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. (f) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585. Ti: (g) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986; chapter 3. (h) Kauffmann, T.; Abel, T.; Li, W.; Neiteler, G.; Schreer, M.; Schwarze, D. Chem. Ber. 1993, 126, 459. Cu: (i) Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Ishihara, Y.; Maruyama, K. J. Org. Chem. 1982, 47, 119. Zn: (j) Gao, Y.; Urabe, H.; Sato, F. J. Org. Chem. 1994, 59, 5521. Sn: (k) Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10356. Pb: (l) Yamamoto, Y.; Yamada, J.-i. J. Am. Chem. Soc. 1987, 109, 4395. Bi: (m) Wada, M.; Ohki, H.; Akiba, K.-y. Tetrahedron Lett. 1986, 27, 4771. Zn/Ti and Zn/Al: (n) Okazoe, T.; Hibino, J.-i.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5581.